1. Field of the Invention
The present invention relates to cinnoline compounds, a process for their preparation, compositions containing these compounds, and a method of regulating the fertility of plants using such compounds.
2. Description of the Background
Although genetic manipulation of plants through cross-breeding is a well-known process, hybrids of self-pollinating plants had been difficult to produce. In some cases, e.g., corn, intensive hand labor is required to prevent self-pollinating but is possible because the male and female flower parts are distant from each other on the corn stalk. However, in other plants, e.g., wheat, the male and female plant parts are contained within the same flower, and self-pollination is difficult if not impossible to prevent. In wheat, the male stamen produces pollen inside a closed flower. The pollen then falls within the closed flower onto the female stigma. Only after this self-pollination step does the flower open to release extra pollen. Mechanical prevention of self-pollination as is practiced in corn is accordingly impossible in a plant such as wheat.
Nevertheless, it is possible to inhibit self-pollination in wheat and similar plants by chemically inhibiting the formation of pollen or by inducing the plant to produce non-functioning pollen. Several compounds have previously been developed which produce these effects.
DOS 28 08 795 discloses compounds of the formula: ##STR2## in which R.sup.1 is carboxy, a carboxy salt, or an alkoxy carbonyl group, R.sup.2 is a substituted phenyl group, R.sup.3 is alkyl, and R.sup.4 is hydrogen, alkyl or halogen. These compounds are disclosed to be pollen suppressants.
Published European Patent Application 0 037 133 discloses compounds of the formula: ##STR3## in which X represents oxygen or sulfur, Y represents hydrogen, halogen or an alkyl group, Z represents an alkyl group, Ar represents an optionally substituted phenyl group, and R represents a group which may be, among others, NR.sup.1 R.sup.2 or ONR.sup.1 R.sup.2 in which R.sup.1 can be hydrogen and R.sup.2 can be an alkoxy group, an acyl group derived from a carboxylic or carbamic acid, or an alkyl group substituted with a carboxylic acid or ester group. These compounds are also disclosed to be pollen suppressants.
Published European Patent Application 0 049 971 discloses compounds of the formula: ##STR4## in which R.sup.1 can be phenyl substituted with a halogen, R.sup.3 can be carboxy or an alkali metal salt thereof, an alkoxy carbonyl, or a substituted carbamoyl, R.sup.5 is a carboxy derivative of the type defined for R.sup.3, and R.sup.6 is a C.sub.1 -C.sub.4 alkyl group. These compounds are disclosed to be chemical hybridizing agents which operate by causing male sterility.
U.S. Pat. No. 4,345,934 discloses a compound of the formula: ##STR5## where Ar is 4-chlorophenyl and an attempt to use this compound as a pollen suppressant. However, this compound was not active as a gametocide.
Zh. Obshch. Khim. (1967) 37:2487, as abstracted in Chem. Abstracts, (1968) 69:36059, discloses a compound of the formula: ##STR6## where Ar is phenyl substituted with halogen. However, this publication is directed only to synthesis and no use for the compound is disclosed.
U.S. Pat. Nos. 4,604,134 and 4,729,782 disclose cinnolines with various substituents and the use of these compounds as chemical pollen suppressants. Some 5-alkoxy- and 5-aminocinnolines are encompassed by the generic formulas set forth in the patents, but such compounds are not emphasized, the preferred compounds being 5-fluorocinnolines. A 6-dimethylaminocinnoline derivative is listed as a typical compound, but no 5-alkoxy- or 5-aminocinnolines or derivatives thereof are specifically listed.
Nevertheless, many of the compounds so far tested have adverse effects on hybrid seed quality or injure plants at doses only slightly above those required to produce maximum male plant sterility. Accordingly, a continued need for new pollen suppressants useful for producing hybrid seed of cereal grain exists.